Following the number one debut of Hollywood's Bleeding in 2019, pretty much everyone wanted
to know one thing: just who is Post Malone dating?
And what does love look like for one of the world's biggest solo artists?
Here's what you might not know about Post Malone's love life.
In 2015, Post Malone was a fresh face in the world of rap, literally.
He didn't even have any face tattoos yet.
At the time, the music star had just released his debut single, "White Iverson," and was
still gearing up to hit the big time.
And although it may not be the case these days, back then he wasn't all that shy about
sharing the details of his relationship with his girlfriend, as he did during a rare joint
appearance on The Breakfast Club.
Like so many of history's great couples, Post Malone and Ashlen Diaz revealed they met each
other at work.
Diaz was a show promoter in Dallas, who previously gave Malone no piece of mind.
Posty, on the other hand, followed Diaz on Instagram pretty much as soon as he could.
Right before he released "White Iverson," she finally followed him back, but they didn't
end up meeting in real life until Diaz booked a show with the rapper.
And as Malone tells it, their first encounter was pretty much as romantic as it gets.
Post said:
"It was snowing, and I just came, and I met her, and I fell in love with this woman."
They officially started dating in February of that year.
Living like an out-of-control rock star couldn't really be further from Post Malone's truth.
Despite some of the more unsavory lyrics of "Rockstar," the rapper claims he was totally
faithful to Diaz while he was on the road.
"It's a wild life, but, you know, the best way to be a good boy is just play Xbox and
keep on my side of the tour bus."
Yes, it seemed like jealousy wasn't the main issue in the pair's relationship, but that
doesn't mean it wasn't without its issues.
In fact, it might have actually been Malone's hectic schedule that finally did them in.
In that same interview, the rapper admitted that balancing work and his romantic life
was one of the biggest difficulties they faced.
"It's always gonna be tough, but if you put in the extra effort, everything works out."
Unfortunately, things didn't work out.
According to Us Weekly, Malone was busy recording his album Hollywood's Bleeding in Utah around
the time that he and Diaz broke up in 2018.
Whether the album caused the split or the split caused the album, however, who can say?
Post Malone's 2016 debut album, Stoney, has some impressive range for a mainstream pop
album.
Instead of focusing purely on relationships, the rapper tackles topics like success, death,
and drug abuse.
Let's be clear, though: it wouldn't be a Post Malone record without a love song or two.
The singer didn't name names, but based on the pair's relationship timeline, it's safe
to assume that Ashlen Diaz was the muse for "Deja Vu," the record's fourth single.
Post revealed the meaning behind the Justin Bieber collaboration in a Genius annotation,
and all signs pointed to Post's lost show promoter.
"I mean, I guess this song is really just me during the beginning stages with starting
to hang out with my girlfriend."
And Posty gave a little insight into he and Diaz's relationship, too, saying,
"It's like, very early stages, but now I've been with her for two years, and you know,
it's cool.
She's annoying, but I love her."
Of course, Ashlen Diaz and Post Malone's relationship wasn't always perfect, and the pair have admitted
that they often ran in circles with their relationship.
Diaz opened up during a Q&A with her fans in June 2018 and admitted that they've even
taken "breaks" from each other before.
But why?
During their joint interview on The Breakfast Club in 2015, a soft-spoken Diaz answered
an uncomfortable question about whether she was nervous that Malone would leave her after
blowing up:
"I mean, yeah, but we have something that's keeping us together."
"You know he's gonna sleep with other women, you do know that?"
At the time, Diaz also revealed that she'd probably forgive the rapper if he cheated
on her, but she wasn't entirely sure, which could potentially explain some of the couple's
alleged on-off behavior later down the line.
Though Post Malone repeatedly shut down any claims that he'd eventually cheat on Diaz,
numerous outlets have since speculated on the possibility.
Reddit has also been buzzing with speculation, including an alleged Instagram screenshot
that pretty much confirms what went down.
Since it's so easy to fake a screenshot, and since Diaz has since deleted a huge chunk
of her social media, however, it's impossible to know what really happened.
Fresh off the heels of a terrifying near-plane crash in August 2018, Post Malone took some
time to relax in the coastal French town of Saint-Tropez.
At the time, the star probably had no idea he was currently embroiled in a Final Destination-like
showdown with destiny, being only weeks away from a car accident, too.
"S--- was scary.
It's very tough stuff."
In fact, it seemed like the only place he was safe was at sea, so maybe it's no surprise
that the singer took to the pristine waters of the Mediterranean to enjoy some downtime
with Ashlen Diaz.
The only problem, was it actually Diaz?
Oddly enough, the Daily Mail simultaneously reported that Malone was spotted on a yacht
in Saint-Tropez with Diaz and without Diaz.
Even The Blast was confused, because the woman in question looked so similar to his longtime
love.
TMZ, which reposted the photos of the musician canoodling with the mystery woman on the boat,
confirmed she was not actually his girlfriend.
However, according to Us Weekly, the headline-making PDA had actually been staged for a music video
shoot.
This one is kind of a head-scratcher, because the yacht doesn't appear in the 2019 music
video for "Saint-Tropez."
So just what really happened there?
Given the on-and-off nature of Post Malone and Ashlen Diaz's relationship, it's hard
to believe that their last breakup was actually their last.
The pair didn't even publicly confirm that they had split, unless you count some vague
references in their now-deleted social media posts.
The most anyone's got to run off of is a source who spoke to Us Weekly, claiming that the
pair broke up in either August or September of 2018.
And that one month is a huge line: it's the difference between Posty possibly cheating
in Saint-Tropez or not.
To make things even more muddled, the sources couldn't even agree on what exactly went down
during the breakup either.
One source told Us Weekly that Diaz pulled the plug, while another said that the split
was mutual.
One of the sources told the outlet:
"Ashlen booked Post a show in Dallas before he was big and knew what she was getting herself
into."
According to the insider, Diaz was pretty upset over their breakup, as just about any
person would be who split up with their boyfriend of three years.
Meanwhile, one Redditor pointed out that Post Malone got his "Ashlen" wrist tattoo covered
up, which would at least give some weight to the rumors.
Sometimes when things don't work out, it's just because they don't work out.
There's no insidious behavior; just two different people.
And from the sounds of it, Post Malone and Ashlen Diaz were pretty different.
One is a shy concert promoter from Dallas, and the other is an outgoing rapper who had
few hesitations about doing...this.
In one of the few Instagram posts Diaz hasn't deleted, the promoter admitted that her shyness
is sometimes painful.
She wrote:
"If you people knew how camera shy I truly am.
Being shy has stopped and limited me from so many opportunities and I'm so tired of
it, but I don't know how I'll actually get over it, I get asked why I never post and
here it is.
I get anxiety and I'm shy."
On the other hand, Post has been busy living like a rock star, which typically involves
parties, events, and pretty much everything a shy person would hate.
An insider told Us Weekly:
"Post loves Ashlen and cares about her, but lives his life as though he's a rock star.
He's still so young."
The real tea with Post Malone's breakup is who got Kylie Jenner in the split.
After all, money can't buy you happiness, but maybe a billionaire BFF can, and Malone
and Ashlen Diaz both appear to be friends with the youngest of the Kardashian-Jenner
sisters.
In annotations on Genius, Post revealed that Jenner was passively responsible for "Fade,"
his 2015 collaboration with Kanye West.
He wrote:
"Kanye liked some of my music.
I met him at Kylie Jenner's party.
She invited me to perform, she's a big fan.
And Kanye was like, 'Let's make something.'"
But it also looks like Diaz is pals with Jenner, and she was spotted hanging out around the
star in the months surrounding her reported breakup.
The promoter posted a snap on Instagram from Kylie Jenner's Barbie-themed 21st birthday
party in August 2019, but Post Malone was nowhere to be found.
Just four days prior, he had been on The Tonight Show With Jimmy Fallon, which tapes in New
York, on the other side of the country.
Earlier that week, he also performed a couple of concerts for Bud Light in the Big Apple.
Is it safe to say Jenner is sticking with her girl in this one?
The mysterious Saint-Tropez woman made her triumphant public return the same month that
Post Malone's split with Ashlen Diaz hit headlines, and this time around, they definitely weren't
filming a music video.
According to TMZ, the pair was spotted holding hands while walking through George Bush Intercontinental
Airport in Houston.
Malone was just about to head to Dubai.
It's unclear if she joined him or not.
In fact, it's still not clear who she is at all.
Per TMZ, things with the mystery girl weren't serious, in fact, apparently they're just
friends.
But who's to say for sure?
And who really holds hands platonically these days?
After hitting the airport with the girl from Saint-Tropez, it seemed like Post Malone managed
to lock up his love life tighter than ever before.
Fans barely heard anything about the star's relationship until months later, when the
typically chill rapper called out some people who were trying to drive a wedge between him
and his girlfriend.
And oh yeah, apparently he now had a girlfriend.
In February 2019, he tweeted:
"To my REAL fans, I love you to death.
To the people trying to dig so f---ing hard to try and get me to leave my girl, y'all
ain't real fans and it needs to stop...Who gives a f---?
Let us live our lives."
According to XXL, this likely had something to do with an online troll who found a personal
Instagram account belonging to the rapper's girlfriend.
She reportedly deactivated her Instagram after it was discovered, but the troll took screenshots
and published them on a different account.
That person allegedly claimed they were trying to bring awareness to the type of person Post's
girlfriend really is.
Post Malone has achieved the almost superhuman feat of being a dude who's constantly in the
tabloids but has nary a photo of himself with his girlfriends.
He managed to take Ashlen Diaz all over on tour, and the only real evidence left of their
relationship is the occasional picture on a friend's Instagram account and her appearances
in a couple of interviews.
When they were dating, they barely posted photos of each other to begin with, probably
because of Diaz's self-admitted camera shyness.
And things don't seem to have changed much.
Today, there's absolutely no concrete evidence that Posty is dating anybody at all.
The last he mentioned having a girlfriend was almost a year ago, which means he could
very well be back on the market.
Alternatively, he could be hiding his relationship from the swarms of paparazzi that constantly
pry into his personal life.
Is he with the girl from Saint-Tropez?
Is there someone new?
Is Austin just focusing on Austin?
Honestly, Post Malone gives his fans enough.
Let him have this one thing for himself.
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